Windward Cay Holidays from NZ$564

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Top Holiday Package Deals in Windward Cay

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek

4 out of 5
Price was NZ$747, price is now NZ$564 per person
NZ$564
per person
27 Apr - 29 Apr
found 1 day ago
Return flight included
Los Angeles (LAX) to Orlando (MCO)
8.8/10 Excellent! (2,794 reviews)
Clean, comfortable room. Excellent staff. Good dining options. Only criticism was that most of the cardio machines in the gym were broken.

Reviewed on 7 Feb 2026

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
Price was NZ$1,434, price is now NZ$880 per person
NZ$880
per person
27 Apr - 29 Apr
found 1 day ago
Return flight included
Los Angeles (LAX) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Great location, property and resort. Had a great time

Reviewed on 6 Feb 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was NZ$873, price is now NZ$682 per person
NZ$682
per person
27 Apr - 29 Apr
found 1 day ago
Return flight included
Los Angeles (LAX) to Orlando (MCO)
9.6/10 Exceptional! (1,002 reviews)
Clean & modern with excellent staff, restaurant & bar!

Reviewed on 5 Feb 2026

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5 out of 5
Save 100% on your flight
Price was NZ$1,991, price is now NZ$1,574 per person
NZ$1,574
per person
27 Apr - 29 Apr
found 1 day ago
Return flight included
Los Angeles (LAX) to Orlando (MCO)
9.2/10 Wonderful! (400 reviews)
This Hotel is Outstanding in every department. Our go to place to bunk down in Orlando’s Disney World & ESPN Wide World Of Sports Venue.

Reviewed on 6 Feb 2026

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
Price was NZ$792, price is now NZ$629 per person
NZ$629
per person
27 Apr - 29 Apr
found 1 day ago
Return flight included
Los Angeles (LAX) to Orlando (MCO)
9.4/10 Exceptional! (1,777 reviews)
Excellent hotel. Great location, super clean, great amenities

Reviewed on 8 Feb 2026

Our guide on where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most. Learn more about Windward Cay
International Drive showing landscape views

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

Find hotels in International Drive District

Our pick of the best Windward Cay Hotel Deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
The price is NZ$245 per night from 2 Mar to 3 Mar
NZ$245
2 Mar - 3 Mar
includes taxes & fees
9.2/10 Wonderful! (4,502 reviews)
Room was very nice, clean and staff was courteous

Reviewed on 4 Feb 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is NZ$475 per night from 3 Mar to 4 Mar
NZ$475
3 Mar - 4 Mar
includes taxes & fees
9.4/10 Exceptional! (3,976 reviews)
Very nice room. Staff was great!

Reviewed on 6 Feb 2026

Hyatt Regency Orlando International Airport
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is NZ$389 per night from 9 Feb to 10 Feb
NZ$389
9 Feb - 10 Feb
includes taxes & fees
8/10 Very Good! (9,021 reviews)
Great service and the place was so clean!! I would stay again. And they upgraded our room from a two-bedroom to a three-bedroom condo!

Reviewed on 5 Feb 2026

The Grove Resort & Water Park Orlando
See all 54,114 properties in Windward Cay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Windward Cay holiday package cost?
Tailor make your Windward Cay holiday package from just NZ$564. Pick from any combination of flights, hotels and rental cars to pull together the trip of your dreams. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Windward Cay?
Bundle your bookings with Expedia to save big on your next getaway. With more than 550 air carriers and 1 000 000 hotels throughout the world, your Windward Cay holiday package can be tailored exactly to suit your budget. With all those extra dollars, why not add one or more interesting experiences and tours? It's an easy way to unlock even more savings. Your dream holiday in Windward Cay is much closer than you thought!
Where should I stay in Windward Cay?
A trip to Windward Cay isn't complete without stopping by Old Town, Fun Spot America and Give Kids the World Village. Spend your evenings near these popular attractions and make sightseeing a breeze.
What are the top hotels in Windward Cay?
Make a reservation at Ref 43 Family Villa With Own Pool Near Disney. It's one of the neighbourhood's most in-demand properties. Another top-rated option in Windward Cay is Lakeside Villa With Perfect Views From Your Private Pool In A Peaceful Community.
How far in advance should I book my Windward Cay holiday?
Reserving your spot early with Expedia means one less thing to worry about. Most air carriers advertise prices up to 12 months prior to departure dates. Usually, this is the cheapest time to book. If circumstances have left you booking late, great deals to Windward Cay will sometimes occur just a few weeks before departure.
What does an Expedia Windward Cay travel package include?
Much of that is up to you. You can select from a variety of Windward Cay packages, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your perfect Windward Cay trip looks like, get set to save!
What should I know before booking a Windward Cay travel package?
Bundling your bookings into a Windward Cay holiday package is the easiest way to organise your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
If I'm not able to travel, can I cancel my Windward Cay holiday package?
Your situation can change unexpectedly, so yes, you can. You may be able to change or cancel your Windward Cay holiday package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, airline or hotel may impose a charge. Need more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Windward Cay

Walt Disney World® Resort

Walt Disney World® Resort

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida™

Universal Studios Florida

An attraction popular with visitors from around the world, where you can wander through film sets and enjoy the thrills and spills of the rides.

Universal Studios Florida
Universal Studios Florida® which includes a city, street scenes and rides

Universal Orlando Resort

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

Activities

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

NZ$47
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

NZ$350
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

NZ$89
per traveller
84% of travellers recommend
Aquatica Orlando
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.